


pretty baby, all dressed up

by Ladyboo



Series: for the sea no longer torments me [1]
Category: Supernatural
Genre: Boys In Love, Coming Out, Crossdressing, Established Dean Winchester/Sam Winchester, M/M, Trans Character, Weecest, Wincest - Freeform
Language: English
Status: Completed
Published: 2018-06-04
Updated: 2018-06-04
Packaged: 2019-05-18 00:43:04
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,470
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14842322
Author URL: https://archiveofourown.org/users/Ladyboo/pseuds/Ladyboo
Summary: Dean didn’t want Sam to ever be ashamed of being beautiful.





	pretty baby, all dressed up

**Author's Note:**

> So, this is a little close to my heart, and I figured I would give it a go. I figure there's going to be some comments on it, so I welcome them, have at, and enjoy~

He didn’t know why he ever believed John on things anymore. 

The man had no real concept of time management, a heavy inability to hold to a simple plan and give Dean a concrete answer on just how long a hunt would take. A ghost, a poltergeist, a simple salt and burn that would take two days, would take two weeks. Would take a month and a half and a state away but he was only seventeen, but he had already dropped out of high school, but he had already left Sam alone for two weeks, nearly three. It set a tension in his bones, a spiral of something panic tight and acid curdle bright in his belly, his lungs, it made him sloppy. 

It made him sloppy and  _ that _ was what John noticed, not that he was tired, not that he was hungry, John noticed that he was  _ distracted _ and that he was  _ getting sloppy _ .

He hadn’t objected, might have played into it a bit, but he caught the wad of cash that John tossed to him from beside his oversized pickup truck and refused to wince at the pull on his bruised ribs. Not in front of John, he needed to stand tall, he needed to be strong, the better he was at hunting meant the longer that Sam didn’t have to, he could take a few bruises and broken bones, he could take another concussion or two. Better him on a hunt, against a wall, in a half-dug grave, receiving John’s heavy handed wrath, better him than Sam, always better him than Sam.

John hadn’t paused though, had just tossed him the money with a few of the fresh cards tucked in and had told him that he’d find them in a little while. 

Except, a little while could mean anything from three days to three months, could mean they had to pack up within an hour of Dean getting back or they had months to themselves, and Dean just-

Dean just stood there, fistful of so much cash he couldn’t actually close his hand around it and watched as John’s truck rumbled down the road and disappeared around a Vermont hill in the dark. A hand smeared across his face and only then did he lean back against the impala, only then did he wince at the blooming ache on his ribs, only then did he let the car take his weary, tired weight as he sagged full body against cool metal. He wanted a nap, knew damn well he could take one in the back of the car and be completely fine if not a little cramped from where his legs had gotten too long. 

But there were nearly six hours between himself and his baby and Sam had been alone almost three weeks. 

So dark he couldn’t see his breath and without the electric glow of John’s headlights illuminating the space around them, he was alone. Nothing but his car and his breathing to keep him company, nothing to separate him from the looming shadow of a farmhouse that hadn’t had its lights on in nearly twenty years. Not since old man Alan had lost his mind in there, not since his wife Clara had cut their children’s throats, he wondered just how long the poltergeist had clung to them, just how much of their minds had been left screaming inside before it had killed them.

He wondered a lot of things, like why John insisted on dragging them into hunts half cocked that were twenty plus miles away from what had been their secondary hunt, the original completed a week ago.

He wondered why John didn’t even seem to care anymore, or if he had ever, foggy memories of laughter he couldn’t quite place and a voice he couldn’t quite hear.

Hand scrubbing across his face, Dean pushed off the car with his elbow, breathed through his teeth with the motion to distribute some of the ache and he yanked open the drivers door with a creaking sound. He needed to oil that, he needed to check her fluids here soon, but for the moment he stuffed the wad of cash into his jacket pocket and shut the door behind him. For now he just slammed her into drive, stomped his foot on the gas with a harsh turn of the wheel, sprayed a cloud of dirt into the air that ate up the glow of his tail lights as he tore off east, opposite how John had gone, as far as he could get from the midnight mourning shell of the Dodson family farmhouse and homeward bound to Sam. 

He had to stop for gas just once, less than five minutes at the pump on the east side of Moscow and Maine was cold in the morning light, spring time chill and he could see his breath, and he stuffed his hands down into the warm pockets of his jacket. John had gone west, possibly south, and there was distance between them now, there was distance and there was quiet and Dean shivered, and Dean curled in on himself a little where he stood at the pump, shoulders loose for the first time in nearly three weeks and his head bowed, quiet, quiet, blissfully quiet. The fuel nozzle had clicked though, tank full, and he’d set it back in its hold before swinging himself back into the impala’s warm interior, before edging out of the lot and hitting the road again. 

Maine rolled past him in the late morning light, 9:30 and the world had already started to wake, people going to their jobs while their children slept in on a Saturday morning. Milo was a small town though, spread out among hills and trees, a quiet kind of soft that they didn’t get to have very often and he was loath to take Sam from this when his brother seemed to have just started to settle in. Fresh air and just melted snow, Sam seemed comfortable here, Sam seemed  _ happy _ here, and that was so rare anymore, he had nearly forgotten what his little brothers smile tasted like. 

They had a house this time, better than the hotel out in Wells, Nevada where John had insisted they wouldn’t spend more than a week, more than a month, where he had watched Sam first turn pink and then golden tan dark beneath the desert winter sun. There wasn’t as much sun now, not the warm kind anyway, spots of clouds and crystal blue, they had a driveway this time. It curled up to the side of the house, weather stained that had once been a clean white probably some thirty years ago, windows with curtains and a second story for all that it was modest. There weren’t any lights on that he could see, but he knew his brother enough to know that Sam wouldn’t be asleep still.

The lock on the front door clicked with his key but the salt line was still intact, long shadows on the floor and no lights apart from where the sun streamed in through the opened curtains. The peaceful quiet of outside had been shattered though as soon as he crossed the threshold, the voice of a woman he didn’t recognize and rifts of a guitar that he didn’t know faintly muffled from somewhere upstairs.

“Sammy?”

The woman wailed on about living on the edge of a broken heart and Dean toed off his boots and left them next to Sams, he crossed the living room to take the stairs two at a time on silent feet. He knew enough to skip the one half way up that creaked, to step wide over the center of the one that liked to scream, and Dean pinwheeled his arms a little at the top where he leaned too far back, compensated until he caught his balance on the landing. 

There was nobody around to see his almost incident or to catch his proud grin but he could hear Sam now. Loud and clear, voice a little high as he sang along with a song that Dean didn’t know. He didn’t know the words but Sam surely did, didn’t miss a single beat, as on tune as he could manage and Dean hesitated there for a verse just to listen.

He crept forward then, silent feet and a curious mind, Sam had taken the upstairs bathroom and Dean would bet his favorite knife that his little brother thought he was still home alone. A side step to avoid the creaking floorboard, a shift of his weight to keep from making a sound, if he did it right, he could sneak up on Sam and what was probably his little brother in a bath. If he did it right, Dean could creep into the bathroom and startle him enough to make him squeal, kiss his parted mouth and grab his sharp little fists before Sam could hit him.

Except, that wasn’t Sam, not really, not like he had expected.

That wasn’t his baby, not like he knew him.

Sam didn’t have hair like that, the color was just a bit too dark, didn’t have the right sun bright highlights to it for all that the length was wrong and it spilled down his back, sleek and straight in a way that Sam’s never was when it got just long enough to try and curl. That was Sam though, he knew those shoulders and he knew those knees, that was his baby with long hair spilling down his shoulders and his spine. 

He had seated himself on the sink, left leg bent and propped up with his foot braced in the basin while the right dangled. The shirt Sam wore was his, Dean recognized the fabric of it, except those were panties, soft and silky looking between thighs that he knew, sunset peach with a hint of white lace and he saw only smooth skin where there should have been a bulge from Sam’s little cock. He stared for a long moment at the nearly flat curve between Sam’s legs, at the sweet, soft peach fabric and the way the hem cinched slightly at his thighs, that was his shirt. That was his shirt that he’d nearly grown out of here recently, too small in the shoulders and it fit Sam just right even if it was a little long. Except, the faded AC/DC logo had a stretch to it, under pressure where it shouldn’t have any, his little brother had the soft, perky swell of tits where he should have had none and Dean’s mouth felt dry. 

A little boombox sat on the closed toilet lid, loud still with the wailing of a woman he didn’t recognize and there was-

There was makeup in the sink. 

There was makeup in the sink and Sam had used it, Sam had used it long enough that he’d gotten fairly skilled at it. Careful color on his face, subtle sweeps of something just a few shades lighter than his skin tone and shimmering bellow his cheekbones. It made his face look sharper, gave him angles where he hadn’t previously had, the wide slash of his mouth had been done in a pretty, wet peach gloss and Dean wanted to taste it, wanted to lick it off of Sam’s lips. Thick lines of black along his upper lids made the sharp slash of his eyes seem heavy lidded, gave him the sort of bedroom eyes that Dean had only seen in magazines before. Made the hazel color look bright, look nearly golden, Sam sat on the sink in pretty panties and a wig and finished his makeup, a sour little open mouthed expression pulling at his wet, glossy lips as he combed mascara onto his lashes with a familiar, steady hand.

Dean had seen him use that sort of focus to clean guns and stitch wounds, but never  _ this. _

He was hard, a heavy, hot, aching weight between his thighs, he was hard and he wanted to touch, wanted to feel, wanted to taste. Sam was soft beneath his hands already, sweet skin and a sugar sticky mouth, Dean knew his kisses like he knew the way his cock slid between Sam’s tight pressed, silken thighs, the way Sam whined and whined and insisted that Dean could fuck him, Dean should fuck him, they didn’t need to wait until he was sixteen. Except Sam was skittish sometimes about things that he would otherwise lean into with a smile, a kiss, and this, this was something he would be skittish about, this was something he would be ashamed of.

Dean didn’t want Sam to ever be ashamed of being beautiful.

Dean didn’t want Sam to ever be ashamed of feeling good about himself. 

Sam hadn’t noticed him though, sticky painted moue still in place and a steady, steady hand pulling the little black brush through his lashes, making them longer, making them pop. Sam hadn’t noticed him and he took a small step back, caught up in the long shift of hair down his brothers back and the sunset peach, sinful stretch of smooth fabric between his thighs.

And he stepped wrong.

And the floorboard beneath him creaked, a loud, groaning sound and he watched as Sam’s shoulders tensed, as his head snapped around. Long hair fluttering, the mascara wand fell into the sink and Sam’s pretty, pretty peach glossed mouth fell open in horror. A sudden drain of color from his face, he looked pale then, he looked scared then, looked as wide eyed as Dean felt. And God, but he looked pretty even there, even with his stricken expression and his clenched fists, Dean wanted to kiss him as much as he wanted to press Sam close and safe to his chest. 

“Sammy-”

Quick movements then, Sam launched himself from the sink with a kind of grace Dean didn’t know he had in his slowly stretching bones. One hand caught the edge of the door and it slammed shut before his bare feet could even touch the floor, Dean could hear him land against it and the lock click into place even as he himself slammed forward. Both hands gripped the doorframe, pressed close where he hadn’t been able to touch Sam, there was nothing on the other side for a few beats of his heart. 

And then there was no music, no more wailing from a woman he didn’t know. No sound of singing to go along with it, none of the little motions of Sam dancing in place where he sat on the sink and instead there was sobbing, he could hear the hiccupping, shuddering sounds of Sam crying. Muffled like his hands were clasped over his mouth, muffled like he had tried to drown himself out with the press of his own skin, his baby was crying with a locked door between them. His baby was breaking down with a wall between them and it felt like a prison then, might as well have been concrete then because Dean couldn’t reach him, Dean couldn’t comfort him.

“Sammy,  _ please _ .”

The sound of the lock sliding into place had been so final, matched the thunder of his heart and the quiet in his head and yet Dean tried the knob anyway. It wouldn’t twist though, wouldn’t turn, and through it he could hear Sam crying, could head his baby sobbing, muffled and quiet but hiccupping and there all the same. Clinging to the doorframe, he was tired to his bones, he wanted to take a shower and maybe sleep, but that was his baby brother in there, that was his  _ baby _ in there. 

He never wanted Sam to be ashamed of himself, never wanted Sam to be  _ scared _ .

Forehead against the door then, Dean sighed, scrubbed a hand over his face and tried to fight the way his throat felt tight at the sound of Sam crying, the way his heart ached. 

“Sam-”

” _ Fuck off!” _

He felt like he was going to be sick.

A clattering sound, running water, Sam was going to take it off. There was no music on the little boom box on the toilet anymore, no happy singing and surely no smile and fuck, that was his heart breaking, wasn’t it? This was his heart breaking, this was panic setting into his bones because he knew how Sam dealt with shame, knew the way his baby would shut down. It wouldn’t exist, the wig would be gone, the makeup lost, the pretty panties left behind, and Sam’s smiles had been tight recently, his expressions pinched. But Sam had looked  _ happy _ , and Dean couldn’t be what ruined that, he couldn’t let that be taken away.

“Sam, don’t!”

“Why  _ not _ , I look like a fre-”

“You look  _ beautiful _ .”

Silence.

Nothing through the door but the slosh of running water, the tremble crackle wet of Sam’s voice rattling around echo sharp between his ears. There was nothing, there was nothing but quiet, but silence, and then-

And then the water turned off. 

The water shut off and he exhaled, a quivering sound, he fell forward a little and braced his forehead against the door. Dean gripped it tight and let his shoulders roll, he listened to quiet sniffling from the other side.

“You think so?”

Muffled by the door then rather than by hands, Sam’s voice was thin, Sam’s voice was wet and small and  _ hopeful _ and Dean had never heard anything so sweet. His smile was strained, desperate as he was sore and as he was tired, and Sam couldn’t see it but he gave it all the same. He wanted to tuck that hair behind Sam’s ears, wanted to hold his pretty, pretty baby and kiss his forehead and tell him everything was okay. 

“You’ve always been pretty Sammy, but you’re beautiful like this. And if you like this, and you wana dress like this? Then good, I think you should if it makes you happy.”

The lock clicked, and it was only his hands on the door jam that kept him from calling forward, kept him from tumbling into the bathroom when the door swung open. It creaked at the hinge, it stuck a bit at the top corner, and Sam peeked out at him from the opening. Black lined eyes and a gloss sticky mouth, his hair was long, spilled over his shoulders and down his front, center parted and sweet, he looked like a girl. He looked like a girl, and there was something in the way that Sam held himself, that maybe-

The door opened the rest of the way and Sam stared up at him, small still, slight still, shirt just a little long around his hips. Long legs there, bare feet there, Sam watched him with wide, liquid eyes and Dean reached out with a slow hand. Gave Sam time to pull away, gave him time to turn his face, but he just leaned forward, just met Dean half way. So one hand cupped his cheek, thumb sweeping across the apple there while the other clung to the doorframe, so he watched as Sam turned his face into the touch, as Sam gave him a thin eyed, sweet smile. 

“You’re okay with it? You still...you still love me, even if I wana be like this?”

His heart clenched, a tight pressure in his chest, a harsh pain along his already aching ribs and the way Dean had meant to press a kiss to Sam’s glossy mouth turned into him pressing their foreheads together instead. He could feel Sam sigh, an exhale against his chin and throat and he smiled, blinked at his little brother and the way Sam watched him. There was a quiet, soft vulnerability there, Sam was scared still, Sam was worried and Dean sighed, Dean angled down enough that he could press their mouths together, so that he could smear Sams sticky peach lip gloss across his own lips. 

Sam though, Sam sagged against him, Sam fisted those little sharp fingered hands in the front of his shirt and held on tight, tried to keep him when he pulled away.

“I will  _ always _ love you, baby girl.”

Sam tasted like peaches, like summertime in Georgia two years back when it had been too hot to do much more than lay on the floor beneath the fan. A soft mouth that Dean knew, he shifted his hand back and soothed his fingers into Sam’s hair, long and loose and sleek and watched Sam’s face. Watched as that pretty, sticky mouth fell open, watched as those bright hazel eyes went wide, as Sam’s pupils blew. 

“I think I like that. I...I think I like that a lot.”


End file.
